Carbon tetrabromide → 3-Nitrophenethyl bromide

HRID 1861910Notes

Reaction equation

HRID 1861910 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[CH2:31]CO)([O-:27])=[O:26]>C(Cl)Cl>[Br:5][CH2:1][CH2:31][C:30]1[CH:29]=[C:28]([N+:25]([O-:27])=[O:26])[CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1040583-Nitrophenylethyl alcohol

Product 1

HCID 5916183-Nitrophenethyl bromideYield 114.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (2.48 g) and triphenylphosphine (2.35 g) were added to a mixture of 3-nitrophenethyl alcohol (1.0 g) and methylene chloride (20 ml) under cooling with ice and stirred for 30 min under cooling with ice. The reaction mixture was distilled under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=4:1) to give 1.58 g of the titled compound quantitatively.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. distillationThe reaction mixture was distilled under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-739ee6139afc4a40811fd81885534aaf
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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